Studies on pyrrolidinones.: Synthesis of new α-pyridones derivatives

被引:10
作者
Malecki, N
Houssin, R
Hénichart, JP
Couturier, D
Petra, F
Legentil, L
Rigo, B
机构
[1] Ecole Hautes Etud Ind, Grp Rech Inhibit Proliferat Cellulaire EA 2692, F-59046 Lille, France
[2] Univ Lille 2, Inst Chim Pharmaceut Albert Lespagnol, Grp Rech Inhibit Proliferat Cellulaire EA 2692, F-59006 Lille, France
[3] Univ Lille 1, Lab Ingn Mol, F-59655 Lille, France
关键词
D O I
10.1002/jhet.5570400105
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dimethyl 7-methoxycarbonylmethyl-5-oxo-1,2,3,5-tetrahydro-indolizine-3,8-dicarboxylate was synthesized starting from methyl pyroglutamate. A study was made of the reactions of this highly functionalized pyridone with ethyl iodide, selenium oxide, isoamyl nitrite and formaldehyde. Literature reports that reaction of 4-(1-carbomethoxypropyl)-5-carbomethoxy-1,6-cyclopentano-2-pyridone with formaldehyde lead to a 95% yield of a monolactone (26) precursor of camptothecin. Our experiments resulted in 15% of this monolactone and 40% of a new dilactone (27).
引用
收藏
页码:45 / 50
页数:6
相关论文
共 61 条
[1]   A short and unequivocal synthesis of 5-aminotetrazolo[1,5-a]quinazoline as a tricyclic analogue of 4-(3-bromoanilino)6,7-dimethoxyquinazoline (PD 153035) [J].
Bencteux, E ;
Houssin, R ;
Henichart, JP .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1997, 34 (04) :1375-1378
[2]  
Bouey-Bencteux E, 1998, ANTI-CANCER DRUG DES, V13, P893
[3]   Studies on pyrrolidinones:: Some attempts to improve the anticancer properties of methyl N-(3,4,4′,5-tetramethoxybenzhydryl)pyroglutamate (HEI 81) [J].
Bourry, A ;
Rigo, B ;
Sanz, G ;
Couturier, D .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (01) :119-124
[4]   Studies on pyrrolidinones:: Some attempts to improve the synthesis of methyl N-(3,4,4′,5-tetramethoxybenzhydryl)pyroglutamate (HEI 81) by using N-acyl iminium salts methodologies. [J].
Bourry, A ;
Pitard, F ;
Rigo, B ;
Sanz, G ;
Camus, F ;
Norberg, B ;
Durant, F ;
Couturier, D .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2002, 39 (01) :109-118
[5]   GAMMA-LACTAM ANALOGS OF CARBAPENEMS [J].
BOYD, DB ;
FOSTER, BJ ;
HATFIELD, LD ;
HORNBACK, WJ ;
JONES, ND ;
MUNROE, JE ;
SWARTZENDRUBER, JK .
TETRAHEDRON LETTERS, 1986, 27 (30) :3457-3460
[6]  
Bryson T. A., 1988, ORG SYNTH, V6, P505
[7]   Synthesis and cytotoxicity of analogues of the antibiotic BE 10988 inhibitors of DNA topoisomerase II [J].
Catrycke, MO ;
Houssin, R ;
Hénichart, JP ;
Pfeiffer, B ;
Renard, P ;
Dassonneville, L ;
Bailly, C .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (14) :2025-2030
[8]   STUDIES ON PYRROLIDONES - CONVENIENT SYNTHESES OF METHYL, METHYL N-METHYLPYROGLUTAMATE AND METHYL N-METHOXYMETHYLPYROGLUTAMATE [J].
CAULIEZ, P ;
RIGO, B ;
FASSEUR, D ;
COUTURIER, D .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (04) :1143-1146
[9]   Practical total synthesis of (+)-camptothecin: The full story [J].
Ciufolini, MA ;
Roschangar, F .
TETRAHEDRON, 1997, 53 (32) :11049-11060
[10]   A 6-STEP SYNTHESIS OF (+/-)-CAMPTOTHECIN [J].
COMINS, DL ;
HONG, H ;
SAHA, JK ;
GAO, JH .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (18) :5120-5121